Ice accumulation poses significant challenges across numerous industries. While dynamic anti-icing surfaces (DAIS) have shown potential in mitigating ice formation and adhesion, their practical use is often limited by the rapid diffusion of liquids and lack of reusability. Overcoming these limitations is crucial to addressing the environmental and economic issues related to ice management. In this study, we introduce a novel approach by incorporating β-cyclodextrin (β-CD) into polydimethylsiloxane (PDMS) silicone rubber, enabling the creation of a sustainable DAIS with the potential of rapid rechargeability. The multiple hydroxyl groups present on the outer surface of β-CD facilitate dipole–dipole interactions and hydrogen bonding, particularly with polar molecules like ethanol and isopropanol. This transforms the surface into a rechargeable system, capable of restoring its low ice adhesion functionality within just 10 min after liquid replenishment. When ice forms on the surface, the system dynamically responds to environmental changes via concentration gradients, controlling the release of liquids and altering surface characteristics. These retained liquids effectively lower the freezing point, melt the ice, and disrupt the ice structure, converting the solid–liquid interface into a liquid–liquid interface. The DAIS effectively alter the ice-substrate interaction and enhance performance at temperatures as low as −18 ℃. By optimizing the β-CD mass ratio and liquid treatments, especially with isopropanol, we achieved an ultra-low ice adhesion strength of 0.6 kPa, which remains stable even after 35 days. This study presents a significant advancement in the development of sustainable, rapidly rechargeable DAIS, offering immense potential for applications in various industries.